Adenosine 5'-monophosphate Property

Melting point:

178-185 °C

Boiling point:

798.5±70.0 °C(Predicted)

Density 

2.32±0.1 g/cm3(Predicted)

FEMA 

4224 | ADENOSINE MONOPHOSPHATE; MONOSODIUM, OR DISODIUM ADENYLATE

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

H₂O: with addition of mild alkalisoluble

form 

Crystalline Powder

pka

3.8, 6.2(at 25℃)

color 

Colorless to white

PH

3.84

Water Solubility 

Soluble in water.

λmax

257 (pH 1)；259 (pH 7)

Merck 

14,158

Stability:

Hygroscopic

InChI

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

InChIKey

UDMBCSSLTHHNCD-KQYNXXCUSA-N

SMILES

P(OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](O)[C@@H]1O)(O)(O)=O

CAS DataBase Reference

61-19-8(CAS DataBase Reference)

EPA Substance Registry System

5'-Adenylic acid (61-19-8)

Safety

Safety Statements 

24/25

WGK Germany 

3

RTECS 

AU7480500

TSCA 

Yes

HS Code 

29389090

Hazardous Substances Data

61-19-8(Hazardous Substances Data)

Toxicity

LD50 intraperitoneal in mouse: 4gm/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

Adenosine 5'-monophosphate Chemical Properties,Usage,Production

Chemical Properties

White crystalline powder. Melting point: 196-200°C (decomposition). Specific optical rotation:-47.5° (20°C, 2% in sodium hydroxide (2%)). Soluble in water, slightly soluble in alcohol, insoluble in ether.

Applications

Clinically it is used to treat disseminated sclerosis, porphyria, itching, liver disease, varicose ulcer complication. Eye drops with denosine monophosphate as the main component can be used to treat eye fatigue, central amphiblestitis, ocular pannus,  herpes and other corneal surface diseases. Intramuscular injection shows local erythema, generalized essential telangiectasia, red face, dizziness, breathing difficulty and palpitation.
As nutrition enhancer; as intermediate to produce nucleotide drugs; as food additive; as biological products; as dietary supplement and biochemical reagent. It is used to produce adenosine triphosphate (ATP), cyclic adenylate (cAMP) and other biochemical drugs. It is a type of nucleotide products and to produce antiviral drugs, synthetic energy drugs and cardiovascular and cerebrovascular drugs, such as adenosine, ATP, 3 '-5'-cyclic adenosine monophosphate.

Preparation

Candida utilis fungi is treated with hot water to obtain nucleic acids, which is hydrolyzed by enzymes and separated to obtain the final product.
Take mycelia as the raw material:
Subtraction and sedimentation of mycelia are carried out with 3 times amount of water. Industry base is added to reach a base concentration of 0.25% (g/100mL). After stirring for 1 hours, 20% sulfuric acid is added until the PH value is 7. The solution is filtrated and the pH value of filtrate is adjusted with 20% sulfuric acid to 2.5. Centrifugation is then applied to obtain nucleic acid mud.
mycelia [sodium hydroxide]→[1h] extract solution [20% sulfuric acid] → [pH=7, filtration] filtrate [20% sulfuric acid] →[pH=2.5, centrifugation] nucleic acid mud
1% nucleic acid solution is made by subsequent dissolution, enzymolysis, absorption and elution. 10% ammonia water is then used to adjust the pH value to 6-6.2. Then the mixture is heated at 90°C for 20 min and cooled. After centrifugation, the supernatant is heated up to 65-70°C and added with 1/3 phosphodiesterase solution. After 2 hours, the temperature is raised to 90°C.  10min later, it is cooled to room temperature. 20% sulfuric acid is added to adjust the pH value to 2.5-3. After filtration, the filtrate is adjusted with ammonia solution until the pH=7.2-7.5. 0.3% (3 g/L) diatomite is then added to assist the filtration. The corresponding supernatant is filtered with an anion exchange resin column (717-type) and eluted with 0.05 mol/L sulfuric acid. Afterwards, absorption, elution and crystallization are carried out. The detailed procedures of these three steps are:
The eluate is first absorbed with a cation exchange column (732-type) and eluted with distilled water (pH=1.5). The collection of eluate starts when the eluate turned red with bromine water. The eluate is then concentrated to 80-90 mg/mL under reduced pressure, added with diatomite and stirred for 30 min before filtration. The filtrate is adjusted with 6 mol/L hydrochloric acid till pH=2.5. To realize full crystallization, the filtrate is cooled during stirring. After followed filtration, it is washed with dry ethanol for 3 times. Vacuum drying at 60°C is applied to obtain the final AMP products.
Nucleic acid mud [ammonia gas] →[pH=6-6.2, 90°C, 20min] supernatant [phosphodiesterase] →[65-70°C,2h,] hydrolysis solution [717 resin] →absorbent [sulfuric acid] →elution solution [732 resin] →AMP, CMP, GMP absorbent mixtures.

Usage restriction

GB 2760-2001：infant formula milk powder 0.2~0.58 g/kg (based on the total amount of nucleotide)

Category

Toxic substance

Toxicity Grading

Middle toxicity

Acute Toxicity

Peritoneal-mouse LD50: 4000 mg/kg

Flammability Hazardous Characteristics

Flammable; generation of toxic nitrogen oxides and phosphorous oxide smoke when heated.

Storage and Transport

Stored in well ventilated area, low temperature, and dry.

Extinguishing Agent

Dry powder, foam, sand, carbon dioxide.

Description

Adenosine-5'-monophosphoric acid is a nucleotide that is synthesized from adenosine triphosphate and inosine monophosphate. Adenosine-5'-monophosphoric acid is an important molecule in the body because it is a substrate for cyclic AMP, which regulates many cellular processes. Adenosine-5'-monophosphoric acid also has biochemical properties that are similar to those of the neurotransmitter serotonin and it can activate the 5-HT2 receptors.

Chemical Properties

colorless to white crystalline powder

Uses

antiasthmatic

Uses

vasodilator, neuromodulator

Uses

Adenosine 5'-Monophosphate is a natural occurring nucleotide and a useful ligand determinant that facilitate the binding of APS reductase inhibitors and activates adenosine receptor agonists.

Uses

A useful ligand determinant that facilitates the binding of APS reductase inhibitors.

Uses

Adenosine 5'-monophosphate is a nucleotide (building blocks of nucleic acid) added to skin care products to bind water and moisture.

Definition

ChEBI: A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.

brand name

Adenyl (Wyeth-Ayerst); My-BDen (Bayer.

Biological Activity

adenosine 5'-monophosphate is an ester of phosphoric acid with the nucleoside adenosine.

Safety Profile

Slightly toxic by intraperitoneal route. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of PO, and NOx.